Don't Be the Worst: How to Date Outside Your Age Range

Whether your love life takes you older or younger, high or Lo, our sex columnist has one guiding principle: Be open to all ages—and closed to the public

I had a game I liked to play with this younger guy, a hilarious invention of my own called "Is He Dead?" It involved talking about living celebrities he was probably too young to remember as though they were already dead, then seeing if he said anything.

Like, "This Cuban-Chinese restaurant is half-Latino, just like the late Emilio Estevez." Or, "I just put a dollar’s worth of O-Town songs in the jukebox. Who knew this bar would have a dollar’s worth of O-Town songs? It’s too bad O-Town was hit by a bus."

He was the only "younger guy" I’d ever gone out with, by about six years, and I used to ask my friends obsessively if it was "weird." But they just thought it was strange that all of our conversations could start a potential death rumor about Ray Liotta. What, after all, had he done?

Ultimately, it wasn’t that this guy was young; it was that I had absolutely nothing to say to him that wasn’t "There," "Not there," "NOT there, this isn’t anybody’s birthday," or "Slow down, Usain Bolt, who incidentally is alive." It wasn’t about age—it was about somebody with a nice body I had absolutely nothing to say to.

I’ve discussed dating out of your demographic with men and women alike, and while everybody has a lot to say on the subject of age, I’m of the opinion that it is, indeed, nothing but a number.

A lot of us have found ourselves attracted to somebody younger or older, and have been reluctant to act on it because of some perceived weirdness or taboo. Some of us limit our potential partners to a very specific age range because that’s what we think we’ll be attracted to. This kind of culling is even easier now that dating sites let us whittle our options down to the year. I contend that as long as nobody is being willfully creepy (I see you, guys in Ferrari hats), this kind of limitation is mega lame.

I know many smoking-hot middle-aged people who are emotional teenagers. I know many brilliant, mature people who aren’t old enough to rent a car. From a sexual attraction standpoint, I challenge you to stand me shirtless next to Sophia Loren in Grumpier Old Men and tell me that a 71-year-old woman can’t be hotter and more charming than some weird 28-year-old, standing next to a television set going, "Hey, can I put this polar fleece back on or what?"

Look, Steely Dan probably couldn’t talk at all to "Hey Nineteen" because they admittedly had "nothing in common." Not because she was too young to name an Aretha Franklin song (which, like, come ON, Steely Dan); the idea that people are what pop culture references they know reduces falling in love to trading trivia. As anybody who’s ever had to play "What are your top five favorite movies?" in a Thai restaurant knows, that’s not love. That’s a bad date.

A lot of women have told me they won’t date younger men because of maturity issues, and that’s probably where the idea of a prohibitive "age gap" comes into play for a lot of people. A fantastic woman several years my senior recently told me I should only date older men, because even though I’m 28, "being in your twenties is a form of functional retardation." I think there’s a grain of truth there, if only because I don’t know anybody who looks back and thinks, "Man, how awesome was I in my twenties?" except for aging pageant queens and John Mellencamp.

But age isn’t maturity. I know this because I once worked with a 42-year-old man who was skipping his daughter’s birthday because "she’ll have one every year, but you never know when they’re going to shut down Burning Man for good."

True, another factor is judgment from other people, who may see a 44-year-old going to dinner with a 25-year-old and make judgments about which one of them is drowning in student loan debt. If only I could tell them how many broke, destitute middle-aged guys I’ve slept with, and challenge their ugly stereotypes. And on the other hand, unless you’re going out with somebody because she’s young, I don’t think it’s cause for judgment. Being predatory is just plain gross on either side of the equation, either from young people looking to trade sex for free Hulu Plus, or old people suffering conversation with somebody who doesn’t even like jazz for the relative elasticity of their genitals.

I don’t have to tell you that the only people who get to decide whether you’re enjoying each other as people are you and your dinner companion. Given the opportunity, your friends and strangers will judge you for being out with somebody who is too fat, too thin, to short, too Asian, too a stripper, whatever. It is up to you to be mutually happy with the person you date. I learned this from experience, but also from Ludacris.

Like height or body type, age is one of those strange things about a person that we know they can’t help, but nevertheless handily use to write them off. If you dismiss people because of their personalities or because you’re on some kind of baby-making timetable, fine, fair enough. But if you’re not into someone because of the arbitrary time in which their parents created them—well, more tasty imperfect flesh for the rest of us.

Admittedly, I prefer older guys, only because they tend to be fully fused, like a human skull. You know generally what you’re going to get from someone by a certain age, because they’ve fully committed to their personalities. The idea that young people like older people because of the financial security is irritating. One, because people who give a fuck about money are awful, and because I’ve met plenty of old, old dudes who are still doing the Somerset Maugham-y cheerful hobo routine.

But, hey, that’s just me. I like the Civil War, documentaries, and talking about whiskey as though it were a zaftig prostitute, so old guys and I get along. The only problem I’ve had with dating outside of my age range is when the other person has been too aware of it. Either he was self-conscious about dating a younger lady, or he tried to pay for everything because he thought I expected it. The only reason a guy is obligated to pay for a woman’s dinner in this day and age is because it’s his turn, it’s her birthday, or because he’s a ma&#xEE;tre d’ who spilled something on her. Women who feel otherwise are the reason we get paid 89 cents to their dollar.

But I realize that I’m a young(ish) woman, and biology is a factor, sure. We still live in an age where men get to age like credenzas, and women like unrefrigerated dairy. I think we can all agree that this is stupid and move on. Some old people are hot, some young people are not. The crotch wants what it wants. I don’t like to think about kids or how old someone will be when I’m 35, because I try not to fixate on a guy’s mortality until after he’s met my parents. Besides, age has nothing to do with lifespan, and we could all get hit by a bus tomorrow, like those poor boys from O-Town.

Remember that game, "Guess Who" ? That is the opposite of what picking a person should be like. When you completely remove personality and individual experience from the equation and rely exclusively on stuff like "young," "blue eyes," and "no glasses," you end up with Robert, that weirdo in the beret. Forget about other people, money, and the looming specter of death. It’s so rare that people meet and like each other. If we start writing people off based on this completely arbitrary Z-factor, we’re really going to end up forcing a lot of conversation with a lot of boring, age-appropriate dullards.

I think that if you meet somebody you like and are attracted to, you meet somebody you like and are attracted to. Go out with people because you want to be naked with them and still hang out with them after. Sure, a lot of compatibility is being at the same place in your life and liking the same things. But while it’s weird to have to affirm that "Pootie Tang was a movie," it’s worth it if the old-ass dude you force to watch it laughs his ass off.

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